Winter’s Utility Boot: The Leather Chukka

A casual and versatile everyday kind of boot

Winter is boot season and there are no shortage of great boot styles. Wingtip dress boots, chelseas, jodhpurs, cap toe dress boots – each very distinctive. But when it comes to a great middle-of-the-road boot style, you can’t beat the classic leather chukka.

leather chukka boots

leather chukka boots

| WEARING | Tommy Hilfiger coat, Ted Baker turtleneck, Michael Andrews Bespoke pants, Drake’s scarf, Leather chukka boots c/o Johnston & Murphy | PHOTOGRAPHY | by Rob McIver Photo

The chukka is an ankle boot with only two or three eyelets. Because of that, they’re typically placed on the more casual end of the boot spectrum and look best paired with either jeans or chinos.

Similar to the desert boot, chukkas come in suede and leather and with a variety of different soles, including crepe, leather or rubber. These are the details that determine the chukka’s “formality tolerance”. A crepe sole would be the most casual, leather most dressy and rubber somewhere in between.

leather chukka boots

When choosing a chukka for your wardrobe, consider what you need them for and when you’d wear them most. These days, because I don’t wear jeans that often and cotton chinos are my “casual” pants, I prefer something on the dressier side.

leather chukka boots

The leather chukka is a great choice for everyday wear and easily dresses up your favorite selvedge denim while pairing seamlessly with chinos or even flannel or tweed trousers (though for flannel and tweed, you might do better with a suede pair).

leather chukka boots

Thanks, as always, for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

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  • Mark Johnson

    That reminds me, I have to get my duffle coat to the cleaners so it’s ready post-holiday.